Nervonic acid: structure, properties, biosynthesis and sources

Chemical structure of nervonic acid

Nervonic acid (24 carbon atoms) was first discovered by Tsujimoto M. in 1927 in fats of Elasmobranch fishes, a subclass of Condroitti class including fishes with fusiform (selachii like sharks from with its first name selacholeic acid) or flatten (batoidea like ray) bodies.
Its structure was established in the same year by Klenk E. who isolated it from cerebrosides of brain tissue.
It is a monounsaturated fatty acids (one cis (Z) double bond, from the methyl end is in n-9 or omega-9 (ω-9) so in shorthand 24:1n-9) member of the sub-group called very long chain fatty acids (VLCFA), from 20 carbon atoms onwards.

Properties of nervonic acid

In purified form, it is a clear to yellowish crystalline powder insoluble in water with melting point at 42.5-43 °C (108.5-109.4 °F; 315.65-316.15 K).

Other names of nervonic acid

selacholeic acid

cis-15-tetracosenoic acid

(15Z)-tetracosenoic acid

(Z)-15-tetracosenoic acid

(15Z)-tetracos-15-enoic acid

cis-delta(15)-tetracosenoic acid

24:1n-9

Biosynthesis of nervonic acid

Fig. 2 – Synthesis of (Z)-tetracos-15-enoic Acid

It is produced fromoleic acid, that undergoes three consecutive chain elongation steps, catalyzed by elongases.
Two carbon units are added in each step, with production of gadoleic acid, erucic acid, and finally, nervonic acid.

Sources of nervonic acid

It occurs as glycerol ester in fish oil like liver oil of spiny dogfish shark (Centrophorus granulosus) and in high amounts (22-25%) in Lunaria annua, a plant of the family of Brassicaceae, synonym Cruciferae.